Preparation and application of alkaline phosphatase activated photosensitizer

A technology of photosensitizer and phosphatase, which is applied in medical preparations containing active ingredients, photodynamic therapy, compounds of Group 5/15 elements of the periodic table, etc., can solve side effects, prolong skin photosensitization, low selectivity, etc. problem, to achieve the effect of avoiding self-absorption, improving photodynamic ability and improving effect

Active Publication Date: 2020-01-07
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the low selectivity of existing photosensitizers, treatment-related tox

Method used

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  • Preparation and application of alkaline phosphatase activated photosensitizer
  • Preparation and application of alkaline phosphatase activated photosensitizer
  • Preparation and application of alkaline phosphatase activated photosensitizer

Examples

Experimental program
Comparison scheme
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Example Embodiment

[0024] Example 1: Synthesis ALP PS-Et

[0025] PS Se-I (0.5g, 0.80mmol) dissolved in acetonitrile (20mL), diethyl chlorophosphate (0.21g, 1.22mmol) and triethylamine (0.12g, 1.2mmol) were added dropwise, the reaction was stirred at room temperature for 5min Later, DMAP (9.8 mg, 0.08 mmol) was added, and stirring was continued overnight at room temperature. After the reaction, the solvent was removed by rotary evaporation, and column chromatography was performed with dichloromethane and methanol as eluents to obtain a bright red solid compound. ALP PS-Et (0.2g, 32.8%). 1 H NMR(400MHz, CDCl 3 ) δ(ppm) 8.76-8.67(m, 1H), 7.99(s, 2H), 7.78-7.68(m, 2H), 7.61-7.51(m, 2H), 7.11(d, J=15.6Hz, 1H) , 6.88 (d, J = 16.0Hz, 1H), 4.43-4.27 (m, 4H), 1.42 (t, J = 7.2Hz, 6H). 13 C NMR(100MHz, CDCl 3 )δ(ppm) 158.51, 152.63, 147.51, 139.23, 135.27, 133.40, 133.29, 131.90, 129.65, 129.45, 129.29, 128.38, 126.82, 124.77, 116.23, 115.03, 89.52, 65.45, 65.39, 16.18, 16.11.

Example Embodiment

[0026] Example 2: Synthesis ALP PS

[0027] ALP PS-Et (0.2g, 0.26mmol) was dissolved in dichloromethane (10mL), trimethylsilyl bromide (1mL) was slowly added dropwise under the protection of nitrogen, and reacted at room temperature for 8h. Filter, rinse the filter residue with dichloromethane (50mL) and dry in a vacuum drying oven to obtain a red solid compound ALP PS (77.8 mg, 42.3%). 1 H NMR(400MHz, DMSO-d 6 )δ(ppm) 8.60(d, J=8.0 Hz, 1H), 8.29(s, 2H), 8.11(d, J=7.2Hz, 1H), 7.86(d, J=16.4Hz, 1H), 7.83( s, 1H), 7.69 (m, 2H), 7.21 (d, J=16.0Hz, 1H). 13 C NMR(100MHz, DMSO-d 6 )δ(ppm) 158.98, 150.55, 139.28, 134.74, 134.19, 132.64, 130.60, 129.63, 128.63, 126.31, 124.22, 117.44, 115.91, 92.31, 71.98. HRMS (ESI): m / z[M+NH + ]calcd for C 20 H 11 I 2 N 3 OSe + 725.8049; found 725.8030.

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Abstract

The invention relates to preparation and application of an alkaline phosphatase activated photosensitizer. The alkaline phosphatase activated photosensitizer is capable of completely inhibiting photosensitivity by ensuring no absorption in visible light spectrum in virtue of ICT effect blockage; and then, when alkaline phosphatase is specifically identified, the ICT effect resumes, so that the photosensitivity is completely released along with recovery of absorption in the visible light spectrum. The strategy facilitates accumulation of the photosensitizer in tumor cells with alkaline phosphatase overexpression; and therefor, curative effects of photodynamics therapy are improved.

Description

technical field [0001] The invention relates to the field of photodynamic therapy, in particular to the preparation and application of an alkaline phosphatase-activated photosensitizer. Background technique [0002] Photodynamic therapy (PDT) is an emerging treatment modality for a variety of cancers. Under light conditions, the photosensitizer is excited to convert triplet oxygen ( 3 o 2 ) into cytotoxic singlet oxygen ( 1 o 2 ), leading to irreversible damage to diseased cells and tissues. However, the low selectivity of existing photosensitizers leads to treatment-related toxicity and side effects on adjacent normal tissues as well as prolonged skin photosensitization. In order to overcome the defects, functional photosensitizers have emerged, which are insensitive in non-cancerous tissues, are activated by interacting with specific biosignaling molecules overexpressed by tumor cells, and efficiently produce 1 o 2 , thereby killing tumor cells. Contents of the in...

Claims

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Application Information

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IPC IPC(8): A61K41/00C07F9/547A61P35/00
CPCA61K41/0057C07F9/547A61P35/00
Inventor 李昌华翟文豪刘明
Owner NANKAI UNIV
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